Synthesis of topsentolides A2 and C2, and non-enzymatic conversion of the former to the latter

Ryo Towada, Shigefumi Kuwahara

研究成果: Article査読

5 被引用数 (Scopus)

抄録

The first total synthesis of the marine-derived cytotoxin topsentolide A2, which eventually culminated in its stereochemical determination, was accomplished in 17 steps from a known chiral alcohol. An improved synthesis of its congener, topsentolide C2, from a synthetic intermediate of topsentolide A2 was also performed by utilizing the Yamaguchi lactonization to construct its nine-membered lactone ring. Treatment of epoxide ring-containing topsentolide A2 with HCl/MeOH brought about its quantitative conversion into topsentolide C2.

本文言語English
ページ(範囲)3774-3781
ページ数8
ジャーナルTetrahedron
70
24
DOI
出版ステータスPublished - 2014 6 17

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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